Common Missteps of First-Time Investors with Stephen Predmore, Ep. 734

Stephen Predmore is the founder and managing partner of Talbott Investments. A former engineer with over 20 years of experience in the manufacturing industry, Stephen transitioned into real estate after a sudden layoff. Since then, he’s grown from single-family investor to general partner in multifamily, specializing in JV structures and educating engineers on passive investing strategies.

 

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📢 Announcement

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Key Takeaways

• Getting laid off inspired Stephen to shift from engineering to real estate investing.

• Initial investments in high-cash-flow rentals revealed the operational challenges of managing tenants and maintenance.

• Transitioning to passive investing provided stronger returns with less stress and time commitment.

• JV deals allow Stephen to combine the benefits of active and passive investing with small groups and creative value-add strategies.

• Engineers often underestimate the time burden of active real estate and over-rely on spreadsheets instead of evaluating lifestyle impact.

 

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Topics

From Layoff to Landlord

• How a sudden post–Super Bowl layoff catalyzed Stephen’s investing journey.

• Lessons learned from early Baltimore rental properties, including eviction challenges and Section 8 issues.

The Case for Passive Investing

• LP investing offers more stability and better returns than small-scale rentals.

• Passive deals free up time while enabling continued W-2 work or other ventures.

• Stephen highlights how his handyman side hustle now fuels his passive portfolio.

JV Deals and Strategic Value-Adds

• Recent acquisitions in West Virginia and Alaska with JV partners.

• Boosting NOI with storage unit additions, washer/dryer installations, and electrical upgrades.

• Investing in red states with favorable landlord laws.

Engineering the Passive Path

• Why professionals—especially engineers—should consider passive syndication investments.

• Real estate isn’t always passive: time cost, emotional stress, and operational friction are often overlooked.

Common Missteps of First-Time Investors

• Underestimating time and headspace costs.

• Taking court battles personally instead of hiring help.

• Forgetting that return on time is just as important as return on capital.

 

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📢 Announcement

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

 

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Round of Insights

Failure that set Stephen up for success: Early struggles managing rentals in Baltimore—evictions, repairs, and stress—led to a smarter pivot to multifamily investing.

Digital/Mobile Resource: Canva — essential for creating content quickly and easily, especially on the go.

Book Recommendation: Who Not How — reading it twice helped him delegate, hire VAs, and focus on high-value tasks.

Daily Habit: Works every